Mac Outlook 2016 login pop3d-ssl merkwürdig

Akinos · Mar 4th 2018

Moin,

ich habe seit ca. einem Jahr ein komisches Login Problem
Rechner ist ein Mac Pro mit Office Home & Business 2016 für Mac (Outlook)

ein normaler pop3d-ssl Login von einem Win 10 oder Win 7 Rechner mit Outlook 2013 oder 2016 auf dem Debian (9) Server schaut so aus:

Feb 5 13:18:56 man1 pop3d-ssl: Connection, ip=[::ffff:2xx.xx.xx.xxx]
Feb 5 13:18:56 man1 pop3d-ssl: LOGIN, user=xxxxxx @ domain. com, ip=[::ffff:2xx.xx.xx.xxx], port=[53719]
Feb 5 13:18:56 man1 pop3d-ssl: LOGOUT, user=xxxxxx @ domain. com, ip=[::ffff:2xx.xx.xx.xxx], port=[53719], top=0, retr=0, rcvd=24, sent=10383, time=0, stls=1

der gleiche Vorgang vom Mac aus wirft dieses Log beim Server raus (Debian 9):

Mar 4 10:48:45 man1 pop3d-ssl: Connection, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:45 man1 pop3d-ssl: The TLS connection was non-properly terminated.
Mar 4 10:48:45 man1 pop3d-ssl: Disconnected, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:45 man1 pop3d-ssl: Connection, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:45 man1 pop3d-ssl: The TLS connection was non-properly terminated.
Mar 4 10:48:45 man1 pop3d-ssl: Disconnected, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:46 man1 pop3d-ssl: Connection, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:46 man1 pop3d-ssl: The TLS connection was non-properly terminated.
Mar 4 10:48:46 man1 pop3d-ssl: Disconnected, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:46 man1 pop3d-ssl: Connection, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:46 man1 pop3d-ssl: The TLS connection was non-properly terminated.
Mar 4 10:48:46 man1 pop3d-ssl: Disconnected, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:46 man1 pop3d-ssl: Connection, ip=[::ffff:2xx.xx.xx.xxx]
Mar 4 10:48:46 man1 pop3d-ssl: LOGIN, user=xxxxxx @ domain. com, iip=[::ffff:2xx.xx.xx.xxx], port=[60570]
Mar 4 10:48:46 man1 pop3d-ssl: LOGOUT, user=xxxxxx @ domain. com, ip=[::ffff:2xx.xx.xx.xxx], port=[60570], top=0, retr=0, rcvd=18, sent=48, time=0, stls=1

kennt jemand dieses Verhalten und kann mir vielleicht sagen wie ich das abstellen kann oder woran das liegt?
Das abfragen der Mails funktioniert ja, nur kommt der Login nicht beim ersten mal zustande

Debian 9
IMSCP 1.5.1
LetsEncrypt Version 3.3.0 (Build 2017070300)
PolicydSPF Version 1.2.0 (Build 2017070300)
PolicydWeight Version 1.2.0 (Build 2017070300)
Postgrey Version 1.2.0 (Build 2017070300)

Mit freundlichen Grüßen

Akinos

**Nuxwin** · Mar 4th 2018

@Akinos

PO server in use: Courier? Dovecot?
Do you use a valid SSL certificate and in mail client, do you use the correct hostname, that is, the one listed in subject alternative name of your SSL certificate?
Error message from your mail client?

Akinos · Mar 4th 2018

Hi nuxwin, first of all thanks for the quick response!

1. Courier
2. Yes, I use a valid SSL cert and use the correct hostname.
3. Fetching mail works eventually, it just takes a lot longer than normal. Outlook on Windows or any other Mail client is much faster and doesn't produce all these failed connections.

I'm happy to provide SSH access to the server if you want to take a closer look.

**Nuxwin** · Mar 4th 2018

@Akinos

Please provide us with error full error message from your mail client.

See also: https://youtrack.i-mscp.net/issue/IP-1401

Akinos · Mar 4th 2018

Hi nuxwin,

I have re-generated the dhparam file as indicated in the ticket, and restarted the mail server. Sadly, it did not resolve the issue for me.

This is a log excerpt from the macOS Console application, which matches the log entries on the server side. Hope this helps - and again, thank you for your assistance.

Code: outlook.log

standard 19:59:49.852507 +0100 Microsoft Outlook TCP Conn [438:0x6000003726c0] using empty proxy configuration
standard 19:59:49.852532 +0100 Microsoft Outlook Stream client bypassing proxies on TCP Conn [438:0x6000003726c0]
standard 19:59:49.852553 +0100 Microsoft Outlook TCP Conn 0x6000003726c0 started
standard 19:59:49.901413 +0100 Microsoft Outlook TCP Conn 0x6000003726c0 event 1. err: 0
standard 19:59:49.901522 +0100 Microsoft Outlook TCP Conn 0x6000003726c0 complete. fd: 54, err: 0
standard 19:59:49.901709 +0100 Microsoft Outlook TCP Conn 0x6000003726c0 starting SSL negotiation
standard 19:59:49.950958 +0100 Microsoft Outlook TCP Conn 0x6000003726c0 SSL Handshake DONE
standard 19:59:50.054862 +0100 Microsoft Outlook TCP Conn 0x6000003726c0 canceled
standard 19:59:50.055684 +0100 Microsoft Outlook TCP Conn [439:0x60c00036a740] using empty proxy configuration
standard 19:59:50.055709 +0100 Microsoft Outlook Stream client bypassing proxies on TCP Conn [439:0x60c00036a740]
standard 19:59:50.055729 +0100 Microsoft Outlook TCP Conn 0x60c00036a740 started
standard 19:59:50.101341 +0100 Microsoft Outlook TCP Conn 0x60c00036a740 event 1. err: 0
standard 19:59:50.101383 +0100 Microsoft Outlook TCP Conn 0x60c00036a740 complete. fd: 54, err: 0
standard 19:59:50.101613 +0100 Microsoft Outlook TCP Conn 0x60c00036a740 starting SSL negotiation
standard 19:59:50.200763 +0100 Microsoft Outlook TCP Conn 0x60c00036a740 SSL Handshake DONE
standard 19:59:50.306844 +0100 Microsoft Outlook TCP Conn 0x60c00036a740 canceled
standard 19:59:50.307651 +0100 Microsoft Outlook TCP Conn [440:0x60c0003642c0] using empty proxy configuration
standard 19:59:50.307712 +0100 Microsoft Outlook Stream client bypassing proxies on TCP Conn [440:0x60c0003642c0]
standard 19:59:50.307751 +0100 Microsoft Outlook TCP Conn 0x60c0003642c0 started
standard 19:59:50.351644 +0100 Microsoft Outlook TCP Conn 0x60c0003642c0 event 1. err: 0
standard 19:59:50.351751 +0100 Microsoft Outlook TCP Conn 0x60c0003642c0 complete. fd: 54, err: 0
standard 19:59:50.351951 +0100 Microsoft Outlook TCP Conn 0x60c0003642c0 starting SSL negotiation
standard 19:59:50.401098 +0100 Microsoft Outlook TCP Conn 0x60c0003642c0 SSL Handshake DONE
standard 19:59:50.507862 +0100 Microsoft Outlook TCP Conn 0x60c0003642c0 canceled
standard 19:59:50.508620 +0100 Microsoft Outlook TCP Conn [441:0x60c000362940] using empty proxy configuration
standard 19:59:50.508646 +0100 Microsoft Outlook Stream client bypassing proxies on TCP Conn [441:0x60c000362940]
standard 19:59:50.508666 +0100 Microsoft Outlook TCP Conn 0x60c000362940 started
standard 19:59:50.552793 +0100 Microsoft Outlook TCP Conn 0x60c000362940 event 1. err: 0
standard 19:59:50.553058 +0100 Microsoft Outlook TCP Conn 0x60c000362940 complete. fd: 54, err: 0
standard 19:59:50.553312 +0100 Microsoft Outlook TCP Conn 0x60c000362940 starting SSL negotiation
standard 19:59:50.600936 +0100 Microsoft Outlook TCP Conn 0x60c000362940 SSL Handshake DONE
standard 19:59:50.707823 +0100 Microsoft Outlook TCP Conn 0x60c000362940 canceled
standard 19:59:50.708443 +0100 Microsoft Outlook TCP Conn [442:0x604000369600] using empty proxy configuration
standard 19:59:50.708468 +0100 Microsoft Outlook Stream client bypassing proxies on TCP Conn [442:0x604000369600]
standard 19:59:50.708490 +0100 Microsoft Outlook TCP Conn 0x604000369600 started
standard 19:59:50.751777 +0100 Microsoft Outlook TCP Conn 0x604000369600 event 1. err: 0
standard 19:59:50.751884 +0100 Microsoft Outlook TCP Conn 0x604000369600 complete. fd: 54, err: 0
standard 19:59:50.752073 +0100 Microsoft Outlook TCP Conn 0x604000369600 starting SSL negotiation
standard 19:59:50.800906 +0100 Microsoft Outlook TCP Conn 0x604000369600 SSL Handshake DONE
standard 19:59:51.401010 +0100 Microsoft Outlook TCP Conn 0x604000369600 canceled

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**Nuxwin** · Mar 4th 2018

Please provide us with the exact parameters you're using in your mail client for the pop3 server connection (a screenshot of your parameters would be welcome (in english)).
Also please make sure that courier-pop-ssl service is running and the result of the following command: netstat -plunt | grep couriertcpd

Akinos · Mar 5th 2018

Hi Nuxwin

root@man1:~# netstat -plunt | grep couriertcpd
tcp6 0 0 :::995 :::* LISTEN 157/couriertcpd
tcp6 0 0 :::110 :::* LISTEN 158/couriertcpd
tcp6 0 0 :::143 :::* LISTEN 174/couriertcpd
tcp6 0 0 :::993 :::* LISTEN 175/couriertcpd

@Nuxwin

I have now taken to test a new I-MSCP
There I have created a new email address and made some pictures
Unfortunately, I have found no option to switch Outlook in English
sorry for my bad english, google translator

step 1

Bildschirmfoto 2018-03-05 um 08.57.36.png

step 2 select pop

Bildschirmfoto 2018-03-05 um 08.58.03.png

step 3

Bildschirmfoto 2018-03-05 um 08.58.31.png

step 4 enter server address and add account

Bildschirmfoto 2018-03-05 um 08.59.png

step 5 check in the console

Bildschirmfoto 2018-03-05 um 09.00.15.png

step 6 check in Outlook

Bildschirmfoto 2018-03-05 um 09.00.png

step 7 change the port in Outlook

Bildschirmfoto 2018-03-05 um 09.01.09.png

step 8 check in the console

Bildschirmfoto 2018-03-05 um 09.01.26.png

greeting Akinos

**momo** · Mar 9th 2018

Hello Akinos, you can experiment with
TLS_CIPHER_LIST=
in /etc/courier/pop3d-ssl

Check out the commented lines in pop3d-ssl for available options

Some lame mail client will require something like

Code

TLS_CIPHER_LIST="ECDH+AESGCM:DH+AESGCM:ECDH+AES256:DH+AES256:ECDH+AES128:DH+AES:ECDH+3DES:DH+3DES:RSA+AESGCM:RSA+AES:RSA+3DES:!aNULL:!MD5:!DSS"

Akinos · Mar 11th 2018

Hi @momo ,

thanks for your suggestion! Sadly, it seems like that wasn't the solution. Both your suggested cipher list as well as the one suggested by Mozilla’s generator ( https://mozilla.github.io/server-side-tls/ssl-config-generator/ ) for „old“ compatibility did not get rid of all the failed connections from Outlook. We even tried allowing TLS_PROTOCOL="SSL3", that didn't help either.

At this point, I have to admit I'm pretty out of ideas. I'll try switching from courier to dovecot later to see if that helps any.

Regards,

Akinos

**Nuxwin** · Mar 14th 2018

Quote from Akinos

Hi @momo ,

thanks for your suggestion! Sadly, it seems like that wasn't the solution. Both your suggested cipher list as well as the one suggested by Mozilla’s generator ( https://mozilla.github.io/server-side-tls/ssl-config-generator/ ) for „old“ compatibility did not get rid of all the failed connections from Outlook. We even tried allowing TLS_PROTOCOL="SSL3", that didn't help either.

At this point, I have to admit I'm pretty out of ideas. I'll try switching from courier to dovecot later to see if that helps any.

Regards,

Akinos

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@flames could you perform some test regarding that issue. ive not the mac client...

Envoyé de mon SM-A510F en utilisant Tapatalk

Mac Outlook 2016 login pop3d-ssl merkwürdig

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